ZA201408071B - Z-selective olefin metathesis catalysts and their synthetic procedure - Google Patents

Z-selective olefin metathesis catalysts and their synthetic procedure

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Publication number
ZA201408071B
ZA201408071B ZA2014/08071A ZA201408071A ZA201408071B ZA 201408071 B ZA201408071 B ZA 201408071B ZA 2014/08071 A ZA2014/08071 A ZA 2014/08071A ZA 201408071 A ZA201408071 A ZA 201408071A ZA 201408071 B ZA201408071 B ZA 201408071B
Authority
ZA
South Africa
Prior art keywords
synthetic procedure
olefin metathesis
metathesis catalysts
selective olefin
selective
Prior art date
Application number
ZA2014/08071A
Inventor
Koji Endo
Myles Benton Herbert
Robert Howard Grubbs
Benjamin Keith Keitz
Paresma Rasiklal Patel
Original Assignee
California Inst Of Techn
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by California Inst Of Techn filed Critical California Inst Of Techn
Publication of ZA201408071B publication Critical patent/ZA201408071B/en

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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2282Unsaturated compounds used as ligands
    • B01J31/2295Cyclic compounds, e.g. cyclopentadienyls
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2265Carbenes or carbynes, i.e.(image)
    • B01J31/2269Heterocyclic carbenes
    • B01J31/2273Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2265Carbenes or carbynes, i.e.(image)
    • B01J31/2278Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02Metathesis reactions at an unsaturated carbon-to-carbon bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046Ruthenium compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543Metathesis reactions, e.g. olefin metathesis alkene metathesis
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261Complexes comprising ligands with non-tetrahedral chirality
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/821Ruthenium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223At least two oxygen atoms present in one at least bidentate or bridging ligand
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22Organic complexes
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/52Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
ZA2014/08071A 2011-01-14 2014-11-04 Z-selective olefin metathesis catalysts and their synthetic procedure ZA201408071B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161432849P 2011-01-14 2011-01-14
US201161433949P 2011-01-18 2011-01-18
US201161515262P 2011-08-04 2011-08-04

Publications (1)

Publication Number Publication Date
ZA201408071B true ZA201408071B (en) 2019-06-26

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Family Applications (2)

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ZA2013/05726A ZA201305726B (en) 2011-01-14 2013-07-29 Z-selective olefin metathesis catalysts and their synthetic procedure
ZA2014/08071A ZA201408071B (en) 2011-01-14 2014-11-04 Z-selective olefin metathesis catalysts and their synthetic procedure

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Country Status (13)

Country Link
US (1) US9597674B2 (en)
EP (1) EP2663398B1 (en)
JP (1) JP5893646B2 (en)
KR (1) KR101835170B1 (en)
CN (1) CN103402628B (en)
AU (1) AU2012206966B2 (en)
BR (1) BR112013017938B1 (en)
CA (1) CA2824518C (en)
IL (1) IL227432A (en)
PL (1) PL2663398T3 (en)
SG (1) SG191980A1 (en)
WO (1) WO2012097379A2 (en)
ZA (2) ZA201305726B (en)

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Publication number Priority date Publication date Assignee Title
EP2838359A4 (en) 2012-03-05 2015-12-09 California Inst Of Techn Syntheses of z-olefin-containing lepidopteran insect pheromones
WO2014001109A1 (en) 2012-06-29 2014-01-03 Apeiron Synthesis S.A. Metal complexes, their application and methods of carrying out of metathesis reaction
US9234985B2 (en) 2012-08-01 2016-01-12 California Institute Of Technology Birefringent polymer brush structures formed by surface initiated ring-opening metathesis polymerization
WO2014022482A1 (en) 2012-08-01 2014-02-06 California Institute Of Technology Solvent-free enyne metathesis polymerization
WO2014093687A1 (en) 2012-12-12 2014-06-19 California Institute Of Technology Z-selective metathesis catalysts
US9663459B2 (en) 2013-04-09 2017-05-30 Materia, Inc. Preparation of surfactants via cross-metathesis
US9663440B2 (en) 2013-04-09 2017-05-30 Materia, Inc. Cross metathesis of poly-branched poly-olefins
US9758445B2 (en) 2013-04-09 2017-09-12 Materia, Inc. Preparation of surfactants via cross-metathesis
US20160101414A1 (en) * 2013-05-15 2016-04-14 California Institute Of Technology Highly z-selective and enantioselective ring opening/cross metathesis catalyzed by a resolved stereogenic-at-ru complex
PL3008078T3 (en) 2013-06-12 2019-06-28 Trustees Of Boston College Catalysts for efficient z-selective metathesis
WO2016014954A1 (en) * 2014-07-25 2016-01-28 California Institute Of Technology Tandem z-selective metathesis / dihydroxylation
WO2017053690A1 (en) * 2015-09-24 2017-03-30 Materia, Inc. Metal carbene olefin metathesis catalysts
WO2017100585A1 (en) 2015-12-10 2017-06-15 Materia, Inc. Olefin metathesis catalysts
CN114106057B (en) * 2016-10-19 2023-06-23 优美科股份公司及两合公司 Synthesis and characterization of Ru alkylene complexes
US10320390B1 (en) 2016-11-17 2019-06-11 X Development Llc Field programmable gate array including coupled lookup tables
US11420926B2 (en) 2017-05-30 2022-08-23 Verbio Vereinigte Bioenergie Ag Methods of making olefinic E- and Z-isomers
MX2020009367A (en) * 2018-03-09 2021-01-15 Ppg Ind Ohio Inc Compounds for coordinating with a metal, compositions containing such compounds, and methods of catalyzing reactions.
JP7368381B2 (en) * 2018-05-15 2023-10-24 カリフォルニア・インスティテュート・オブ・テクノロジー Total synthesis of prostaglandin J natural products by steric preservation metathesis
US11939410B2 (en) * 2018-06-29 2024-03-26 Apeiron Synthesis S.A. Organoruthenium complexes as precatalysts for olefin metathesis
EP3999230A1 (en) * 2019-07-17 2022-05-25 California Institute of Technology New syntheses of z-selective olefin metathesis catalysts
CN114478166A (en) * 2020-10-26 2022-05-13 中国石油天然气股份有限公司 Method for preparing terminal olefin

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US5312940A (en) 1992-04-03 1994-05-17 California Institute Of Technology Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
US6284852B1 (en) * 1997-10-30 2001-09-04 California Institute Of Technology Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
AU2001284773B2 (en) 2000-08-10 2004-08-05 Trustees Of Boston College Recyclable metathesis catalysts
US6620955B1 (en) 2001-11-15 2003-09-16 Richard L. Pederson Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
AU2003221674A1 (en) * 2002-04-05 2003-10-27 California Institute Of Technology Cross-metathesis of olefins directly substituted with an electron-withdrawing group using transition metal carbene catalysts
ZA200700170B (en) * 2004-06-09 2008-05-28 Uti Limited Partnership Transition metal carbene complexes containing a cationi substituent as catalysts of olefin metathesis reactions
FR2878246B1 (en) 2004-11-23 2007-03-30 Inst Francais Du Petrole PROCESS FOR CO-PRODUCTION OF OLEFINS AND ESTERS BY ETHENOLYSIS OF UNSATURATED FATTY BODIES IN NON-AQUEOUS IONIC LIQUIDS
EP2886549A1 (en) * 2005-07-04 2015-06-24 Zannan Scitech Co., Ltd. Ruthenium complex ligand, ruthenium complex and the use of the complex as a catalyst in olefin metathesis reactions
US8877936B2 (en) * 2008-04-09 2014-11-04 California Institute Of Technology Ruthenium olefin metathesis catalysts bearing N-heterocyclic carbene ligands with substituted backbone
EP2255877B1 (en) * 2009-05-07 2014-09-24 Umicore AG & Co. KG Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands

Also Published As

Publication number Publication date
IL227432A0 (en) 2013-09-30
CA2824518C (en) 2019-03-26
SG191980A1 (en) 2013-08-30
WO2012097379A3 (en) 2012-10-11
BR112013017938A2 (en) 2018-11-27
IL227432A (en) 2017-12-31
CN103402628A (en) 2013-11-20
JP2014503356A (en) 2014-02-13
AU2012206966B2 (en) 2016-11-17
CA2824518A1 (en) 2012-07-19
WO2012097379A2 (en) 2012-07-19
CN103402628B (en) 2015-12-23
KR101835170B1 (en) 2018-03-06
US20140106960A1 (en) 2014-04-17
EP2663398A2 (en) 2013-11-20
BR112013017938B1 (en) 2019-10-15
EP2663398B1 (en) 2018-07-18
US9597674B2 (en) 2017-03-21
ZA201305726B (en) 2018-12-19
JP5893646B2 (en) 2016-03-23
EP2663398A4 (en) 2014-07-23
PL2663398T3 (en) 2019-01-31
KR20140021995A (en) 2014-02-21

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